Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treatestablished illnesses. It is synthesized from adamantane by the following sequence:Br2(1)BrAdamantane1-bromoadamantaneCH,—CHBrAlBr3(3)(2)Br-BrNH₂(5)(4)Rimantadinea Step 2 proceeds via the following mechanism:1. AlBra acts as a Lewis acid to yield carbocation 1;2. Bromoethene acts as a nucleophile to give carbocation 2:3. Carbocation 2 reacts with nucleophile 3 to give the product of reaction 2.Work out this mechanism on a separate sheet of paper and then draw the structure of nucleophile 3.

Experimental condition to achieve step 3 product would be by reacting with sodium amide in the…

Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat established illnesses. It is synthesized from adamantane by the following sequence: Br₂ 0 (1) -Br 1-bromoadamantane Adamantane CH,—CHBr AlBr3 (2) Br -Br

Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat established illnesses. It is synthesized from adamantane by the following sequence: Br₂ 0 (1) -Br 1-bromoadamantane Adamantane CH,—CHBr AlBr3 (2) Br -Br

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter7: Alkynes

Section: Chapter Questions

Problem 7.19P

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